Cesium carbonate → Tert-butyl 2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a mixture of tert-butyl 1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (I-11, 80.0 g, 315 mmol) and 4-methyl-5-oxo-2,5-dihydrofuran-3-yl trifluoromethanesulfonate (I-9, 85.2 g, 346 mmol), Xantphos (13.6 g, 23.6 mmol), Cs2CO3 (153.7 g, 471.8 mmol) in toluene (1200 mL), was added Pd2(dba)3 (7.20 g, 7.86 mmol) under N2. The resulting reaction mixture was heated to 90° C. and stirred under N2 for 18 h. The mixture was filtered through a pad of CELITE® and the filtrate was concentrated. The residue was purified by precipitation to give tert-butyl 2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate. 1H NMR (400 MHz, CDCl3) δ 5.23 (s, 2H), 4.02-3.99 (m, 4H), 3.06-3.05 (m, 2H), 2.15-2.11 (m, 2H), 2.02 (s, 3H), 1.87-1.81 (m, 2H), 1.51-1.41 (m, 11H)

Provenance & Evidence